There’s an art to asking thought-provoking questions without seeming too intense, cheesy, or inauthentic. It starts with having a genuine interest in this new person, making eye contact, and responding appropriately to their answers. Toss out the comments about the weather and try these meaningful questions instead.
1. How did you hear about this event?
This is an easy one to get started with. Yes, it’s basic but the answer will give you a lot to work with. If they know the host, found out about it in a certain group, or go to it every month, use that newfound knowledge to dig deeper.
2. What’s the coolest/funniest/scariest/most interesting thing that’s happened to you at work?
Everyone has an interesting job, and we often meet with people who work in the same industry but in a different sector. Sure, you’re both photographers, but you specialize in weddings and they do pets. It’s a good opportunity to hear their side of the story, bring out their personality, and begin the exchange of really friendly banter that is work related but more humanizing.
3. What did you do before this?
This question helps you to know who they are. Have they always been in this industry? Have they jumped around? Did you both possibly work for the same company at different times? If you want to make things even more interesting, encourage them to start with their very first job to give the conversation a more light-hearted appeal.
4. When did you know that this was your calling?
This one is a more thoughtful question that can be asked deeper into the conversation and will help your new acquaintance be honest with you. Be prepared to receive answers from all over the spectrum, including a detailed story of how they’ve been doing this since the day they were born to a hesitant, short answer of how they still aren’t sure this is “the one.” Either way, use that moment as a place to relate and/or commiserate.
5. What are you reading or listening to right now?
I absolutely love this question. It’s updated with “listening” thanks to the audio book and podcast era, but it helps you understand their interests and selfishly allows you to add some good content to your list. Plus, it’s such a good way to connect with someone, especially if you’ve both read or listened to the same thing. Whether you can start discussing a podcast episode or a book theory, you’re already on your way to forging a true connection with this former stranger.
At the end of the day, network with your new acquaintance in mind. Let them do the talking and challenge yourself to drive the conversation toward an authentic and meaningful place.